MXPA05000033A - Utilizacion de carboxamida de heteroareno como ligandos de dopamina-d3 para el tratamiento de enfermedades de cns. - Google Patents
Utilizacion de carboxamida de heteroareno como ligandos de dopamina-d3 para el tratamiento de enfermedades de cns.Info
- Publication number
- MXPA05000033A MXPA05000033A MXPA05000033A MXPA05000033A MXPA05000033A MX PA05000033 A MXPA05000033 A MX PA05000033A MX PA05000033 A MXPA05000033 A MX PA05000033A MX PA05000033 A MXPA05000033 A MX PA05000033A MX PA05000033 A MXPA05000033 A MX PA05000033A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- hydrogen
- cyano
- halogen
- alkynyl
- Prior art date
Links
- -1 heteroarene carboxamide Chemical class 0.000 title claims abstract description 82
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 35
- 201000010099 disease Diseases 0.000 title claims description 7
- 239000003446 ligand Substances 0.000 title description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 79
- 208000035475 disorder Diseases 0.000 claims abstract description 28
- 125000001424 substituent group Chemical group 0.000 claims abstract description 26
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims abstract description 17
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 16
- 208000010118 dystonia Diseases 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims abstract description 15
- 208000012661 Dyskinesia Diseases 0.000 claims abstract description 14
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims abstract description 14
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 14
- 208000014094 Dystonic disease Diseases 0.000 claims abstract description 13
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 8
- 101710155073 2-amino-3,7-dideoxy-D-threo-hept-6-ulosonate synthase Proteins 0.000 claims abstract description 7
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 7
- 208000005793 Restless legs syndrome Diseases 0.000 claims abstract description 7
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- 229960003920 cocaine Drugs 0.000 claims abstract description 7
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 7
- 208000013403 hyperactivity Diseases 0.000 claims abstract description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
- 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 7
- 206010008531 Chills Diseases 0.000 claims abstract description 6
- 208000031424 hyperprolactinemia Diseases 0.000 claims abstract description 4
- 208000015114 central nervous system disease Diseases 0.000 claims abstract 2
- 210000002265 sensory receptor cell Anatomy 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 79
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 77
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 150000002367 halogens Chemical group 0.000 claims description 62
- 229910052736 halogen Chemical group 0.000 claims description 61
- 125000002252 acyl group Chemical group 0.000 claims description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 55
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000000304 alkynyl group Chemical group 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 31
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- 229940124597 therapeutic agent Drugs 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 230000003137 locomotive effect Effects 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
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- 229940079593 drug Drugs 0.000 claims description 8
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 6
- 206010012335 Dependence Diseases 0.000 claims description 6
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- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 6
- 229960001027 opium Drugs 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229960004502 levodopa Drugs 0.000 claims description 4
- 238000002679 ablation Methods 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- KNEXGVPHPGXAGF-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical group C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 KNEXGVPHPGXAGF-UHFFFAOYSA-N 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
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- 206010057852 Nicotine dependence Diseases 0.000 abstract 1
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
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- 239000011780 sodium chloride Substances 0.000 description 15
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 13
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 12
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- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 10
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- 238000002474 experimental method Methods 0.000 description 9
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- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10230062 | 2002-07-04 | ||
| DE10232020A DE10232020A1 (de) | 2002-07-04 | 2002-07-10 | Neurorezeptoraktive Heteroarencarboxamide |
| PCT/EP2003/007060 WO2004004729A1 (de) | 2002-07-04 | 2003-07-02 | Heteroarencarboxamide zur verwendung als dopamin-d3 liganden zur behandlung von zns-erkrankungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05000033A true MXPA05000033A (es) | 2005-04-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05000033A MXPA05000033A (es) | 2002-07-04 | 2003-07-02 | Utilizacion de carboxamida de heteroareno como ligandos de dopamina-d3 para el tratamiento de enfermedades de cns. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20050197343A1 (https=) |
| EP (1) | EP1519726B1 (https=) |
| JP (1) | JP2005538974A (https=) |
| KR (1) | KR20050075281A (https=) |
| CN (1) | CN1665503A (https=) |
| AT (1) | ATE354367T1 (https=) |
| AU (1) | AU2003246356A1 (https=) |
| CA (1) | CA2489396A1 (https=) |
| DE (1) | DE50306588D1 (https=) |
| DK (1) | DK1519726T3 (https=) |
| ES (1) | ES2280799T3 (https=) |
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| RU (1) | RU2320656C2 (https=) |
| WO (1) | WO2004004729A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| SE521512C2 (sv) * | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| ES2285233T3 (es) | 2002-12-20 | 2007-11-16 | Niconovum Ab | Un material en particulas que contiene nicotina y celulosa microcristalina fisicamente y quimicamente estable. |
| DE102004037445A1 (de) * | 2004-08-02 | 2006-03-16 | Schwarz Pharma Ag | Carboxamide des Indolizins und seiner Aza- und Diazaderivate |
| DE102004054634A1 (de) * | 2004-11-12 | 2006-05-18 | Schwarz Pharma Ag | Azaindolcarboxamide |
| DE102004063797A1 (de) * | 2004-12-30 | 2006-07-13 | Schwarz Pharma Ag | Sauerstoffhaltige annelierte Phenylpiperazin- und Phenyldiazepancarboxamide |
| CA2593266A1 (en) * | 2005-01-03 | 2006-07-13 | Universita Degli Studi Di Siena | Aryl piperazine derivatives for the treatment of neuropsychiatric disorders |
| US9402809B2 (en) | 2006-03-16 | 2016-08-02 | Niconovum Usa, Inc. | Snuff composition |
| FR2903986A1 (fr) * | 2006-07-21 | 2008-01-25 | Pierre Fabre Medicament Sa | Nouveaux derives chromenes ou thiochromenes carboxamides, leur procede de preparation et leurs applications en therapeutique |
| WO2008153573A1 (en) * | 2007-06-15 | 2008-12-18 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | 4-phenylpiperazine derivatives with functionalized linkers as dopamine d3 receptor selective ligands and methods of use |
| US9227944B2 (en) | 2008-10-10 | 2016-01-05 | Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China | Dopamine D3 receptor ligands and preparation and medical uses of the same |
| JP5701213B2 (ja) * | 2008-10-10 | 2015-04-15 | インスティチュート オブ ファーマコロジー アンド トキシコロジー アカデミー オブ ミリタリー メディカル サイエンシズ ピー．エル．エー．チャイナ | 新規なドーパミンｄ３受容体リガンド、その調製及び使用 |
| FR2949465B1 (fr) * | 2009-09-01 | 2011-08-12 | Pf Medicament | Derives chromones, leur procede de preparation et leurs applications therapeutiques |
| US11299476B2 (en) | 2016-03-14 | 2022-04-12 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Dopamine D3 receptor selective antagonists/partial agonists; method of making; and use thereof |
| SI3429993T1 (sl) | 2016-03-14 | 2021-09-30 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services, National Institutes Of Health, Office Of Technology Transfer | Selektivni antagonisti/delni agonisti dopaminskega receptorja D3; postopki izdelave; in uporaba le-teh |
| EP3849963A1 (en) | 2018-09-11 | 2021-07-21 | The United States of America, as Represented By the Secretary, Department of Health and Human Services | Dopamine d3 receptor selective antagonists/partial agonists and uses thereof |
| CN114409621B (zh) * | 2022-02-09 | 2023-09-08 | 江苏省原子医学研究所 | 一种靶向多巴胺d3受体的诊疗药物及其应用 |
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| US3646048A (en) * | 1970-02-02 | 1972-02-29 | American Cyanamid Co | N-(tert-aminoalkyl)-2-indenecarboxamides |
| US3646047A (en) * | 1970-02-02 | 1972-02-29 | American Cyanamid Co | Certain benzo(b)thiophene-2-carboxamide derivatives |
| NL8005133A (nl) * | 1980-09-12 | 1982-04-01 | Duphar Int Res | Fenylpiperazinederivaten met antiagressieve werking. |
| IL90279A (en) * | 1988-05-24 | 1995-03-30 | American Home Prod | Piperazinyl carboxamide derivatives, their preparation and pharmaceutical com¦ositions containing them |
| US5106849A (en) * | 1988-05-24 | 1992-04-21 | American Home Products Corporation | Use of aryl- and heteroaryl piperazinyl carboxamides in the treatment of various central nervous system disorders |
| ES2027898A6 (es) * | 1991-01-24 | 1992-06-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados de la 2-metoxifenilpiperacina. |
| SE9201138D0 (sv) * | 1992-04-09 | 1992-04-09 | Astra Ab | Novel phthalimidoalkylpiperazines |
| DE4425146A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
| EP0891344B1 (fr) * | 1996-04-05 | 2002-12-18 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Antagonistes du recepteur alpha-1 adrenergique |
| HUP0103987A3 (en) * | 2001-09-28 | 2004-11-29 | Richter Gedeon Vegyeszet | Phenylpiperazinylalkyl carboxylic acid amid derivatives, process for their preparation, pharmaceutical compositions containing them and their intermediates |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20050075281A (ko) | 2005-07-20 |
| AU2003246356A1 (en) | 2004-01-23 |
| US20050197343A1 (en) | 2005-09-08 |
| WO2004004729A1 (de) | 2004-01-15 |
| ES2280799T3 (es) | 2007-09-16 |
| ATE354367T1 (de) | 2007-03-15 |
| RU2320656C2 (ru) | 2008-03-27 |
| CN1665503A (zh) | 2005-09-07 |
| PL374612A1 (en) | 2005-10-31 |
| EP1519726B1 (de) | 2007-02-21 |
| EP1519726A1 (de) | 2005-04-06 |
| CA2489396A1 (en) | 2004-01-15 |
| NO20050386L (no) | 2005-01-25 |
| JP2005538974A (ja) | 2005-12-22 |
| IL165677A0 (en) | 2006-01-15 |
| RU2004139041A (ru) | 2005-07-20 |
| DK1519726T3 (da) | 2007-06-04 |
| HK1074579A1 (en) | 2005-11-18 |
| DE50306588D1 (de) | 2007-04-05 |
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